1-(2-fluorophenyl)-1H-indazole | 1417198-45-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2-fluorophenyl)-1H-indazole
• 英文别名: 1-(2-Fluorophenyl)indazole
• CAS: 1417198-45-8
• 化学式: C₁₃H₉FN₂
• 分子量: 212.226
• InChiKey: XEVBGEMPQIWFAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-fluorophenyl)-1H-indazole 、 四苯硼钠 、 硫酸二甲酯 以 甲苯 、 水 为溶剂， 反应 24.0h， 以83%的产率得到1-(2-fluorophenyl)-2-methyl-1H-indazol-2-ium tetraphenylborate
  参考文献：
  名称：

  Syntheses of Acridines and Quinazoline-2,4(1H,3H)-dithiones by Rearrangements of N-Heterocyclic Carbenes of Indazole

  摘要：

  N-Heterocyclic carbenes of indazole which are arylated at N1 (1-aryl-indazol-3-ylidenes) have been generated by deprotonation of the corresponding indazolium salts. On deprotonation with potassium carbonate, potassium phosphate or tert-butanolate in dioxane or toluene at reflux temperature, a rearrangement to acridines took place. Deprotonation with n-butyllithium in THF at room temperature in the presence of carbon disulfide gave quinazoline-2,4(1H,3H)-dithiones by a new rearrangement reaction.

  DOI：

  10.3987/com-14-13082
• 作为产物：
  描述：

  在 铜 、 sodium t-butanolate 作用下， 反应 20.0h， 以76%的产率得到1-(2-fluorophenyl)-1H-indazole
  参考文献：
  名称：

  Copper Powder–Catalyzed C-N Bond Formation of Arylhydrazones of 2-Bromobenzaldehydes Leading to 1-Aryl-1H-indazoles

  摘要：

  Arylhydrazones of 2-bromobenzaldehydes and its analogs are cyclized in PEG-400 at 110 degrees C in the presence of a catalytic amount of copper powder along with NaOtBu to give 1-aryl-1H-indazole derivatives in good yields.

  DOI：

  10.1080/00397911.2011.614714

文献信息

• A ligand-free copper-catalyzed strategy to the N-arylation of indazole using aryl bromides
  作者：Di-Xiang Bai、Rachel Sin-Ee Lim、Hui-Fen Ng、Yong-Chua Teo

  DOI：10.1080/00397911.2021.1883062

  日期：2021.5.3

  Abstract A simple and efficient strategy for the C–N cross-coupling of indazole with a variety of substituted aryl bromides is reported. Under the optimized conditions, a broad scope of N-arylated products were obtained in good to excellent yields (up to 87%) under the ligand-free conditions.

  摘要 据报道，一种简单有效的方法使吲唑与各种取代的芳基溴化物进行C–N交叉偶联。在最优化的条件下，在无配体的条件下，可以以良好至极好的收率（高达87％）获得宽范围的N-芳基化产物。
• Copper(I) salt/PEG-400 catalysis in one-pot direct synthesis of 1-aryl-1<i>H</i>-indazoles from 2-bromobenzaldehydes and arylhydrazines
  作者：Yeon Kyu Bae、Chan Sik Cho

  DOI：10.1002/aoc.2956

  日期：2013.4

  2‐Bromobenzaldehydes are condensed and cyclized with arylhydrazines (or their hydrochlorides) in PEG‐400 at 110 °C in the presence of a catalytic amount of a copper(I) salt along with a base to give 1‐aryl‐1H‐indazoles in high yields. Copyright © 2013 John Wiley & Sons, Ltd.

  将2-溴苯甲醛在催化量的铜（I）盐和碱存在下于110°C下与芳肼（或其盐酸盐）缩合并与PEG-400环合，得到1-芳基-1 H吲唑高产。版权所有©2013 John Wiley＆Sons，Ltd.
• INDAZOLE COMPOUNDS AS CCR1 RECEPTOR ANTAGONISTS
  申请人：Boehringer Ingelheim International GmbH

  公开号：EP2285783A1

  公开（公告）日：2011-02-23
• Syntheses of Acridines and Quinazoline-2,4(1H,3H)-dithiones by Rearrangements of N-Heterocyclic Carbenes of Indazole
  作者：Andreas Schmidt、Zong Guan、Mimoza Gjikaj

  DOI：10.3987/com-14-13082

  日期：——

  N-Heterocyclic carbenes of indazole which are arylated at N1 (1-aryl-indazol-3-ylidenes) have been generated by deprotonation of the corresponding indazolium salts. On deprotonation with potassium carbonate, potassium phosphate or tert-butanolate in dioxane or toluene at reflux temperature, a rearrangement to acridines took place. Deprotonation with n-butyllithium in THF at room temperature in the presence of carbon disulfide gave quinazoline-2,4(1H,3H)-dithiones by a new rearrangement reaction.
• Copper Powder–Catalyzed C-N Bond Formation of Arylhydrazones of 2-Bromobenzaldehydes Leading to 1-Aryl-1<i>H</i>-indazoles
  作者：Hye Kyung Lee、Chan Sik Cho

  DOI：10.1080/00397911.2011.614714

  日期：2013.2.1

  Arylhydrazones of 2-bromobenzaldehydes and its analogs are cyclized in PEG-400 at 110 degrees C in the presence of a catalytic amount of copper powder along with NaOtBu to give 1-aryl-1H-indazole derivatives in good yields.